stereoselective synthesis of a new cis monocyclic β-lactam bearing a sugar moiety at its n1 position and its physical characterization立体选择合成一个新的独联体单环β-lactam轴承糖基n1位置和其物理特性.pdfVIP

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stereoselective synthesis of a new cis monocyclic β-lactam bearing a sugar moiety at its n1 position and its physical characterization立体选择合成一个新的独联体单环β-lactam轴承糖基n1位置和其物理特性.pdf

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stereoselective synthesis of a new cis monocyclic β-lactam bearing a sugar moiety at its n1 position and its physical characterization立体选择合成一个新的独联体单环β-lactam轴承糖基n1位置和其物理特性

M544 Stereoselective Synthesis of a New Cis Mono yclic βlactam B... Molbank 2007, M544 /molbank/ Stereoselective Synthesis of a ew cis Monocyclic βlactam Bearing a Sugar Moiety at Its 1 Position and Its Physical Characterization 1,* 2 1 Aliasghar Jarrahpour , Abraham F. Jalbout and Parvaneh Alvand 1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran 2. Department of Chemistry, University of Arizona, Tucson, AZ 85721 USA * Author to whom correspondence should be addressed. Tel: + 98 711 2284822; Fax: +98 711 2280926; Email: jarrah@susc.ac.ir Received: 29 December 2006 / Accepted: 27 February 2007 / Published: 30 May 2007 Keywords: 2azetidinone, phenoxy ketene, asymmetric synthesis, chiral Schiff bases, sugar, [2+2] cycloaddition. Abstract: Synthesis of a new monocyclic βlactam containing a sugar moiety at its N1 position via [2+2] cycloaddition reaction of ketene and imine is described. Reaction of achiral phenoxy ketene with chiral aldimine derived from chiral 2, 3, 4, 6tetraOacetylβDgalactopyranosylamine and 2hydroxy3methoxy benzaldehyde resulted in the formation of 2 as a single diastereomer. Then its physical characterization has been determined at the AM1 level of theory. Introduction OAcylprotected glycosylamines and their imine derivatives, particularly the 2,3,4,6tetraOpivaloyl Dgalactopyranosylamine and its acetyl derivative are effective chiral auxiliaries in Strecker and Ug